This invention relates generally to organopolysiloxane compounds which contain modified silicon-bonded N-(aminohydrocarbyl)-aminohydrocarbyl radicals (herein also diamine radicals) and to a process for their preparation. More specifically, the present invention relates to organopolysiloxane compounds which contain silicon-bonded acylated diamine radicals and to an acylating process for their preparation.
Organopolysiloxane compounds which contain silicon-bonded N-(aminohydrocarbyl)-aminohydrocarbyl radicals are well known in the organosilicon art. They have found utility as precursors to other organopolysiloxane compounds, as components in textile treating baths and hair care compositions and as curable compositions, owing in large part to the chemical reactivity of the diamine radicals that are present therein. However, for many uses the chemical reactivity of said diamine radicals is not suitable and attempts to modify the diamine radicals have been made.
Gilkey et al. and Krahnke have reacted urea with an organopolysiloxane bearing diamine radicals to provide organopolysiloxanes bearing various degrees of uriedo-substitution. U.S. Pat. Nos. 3,209,053; 3,702,860 and 3,772,351. The resulting organopolysiloxanes were useful as a reactive component in textile-treating formulations that also contained urea-based resins.
Martin, U.S. Pat. No. 4,390,713, teaches that aminofunctional polysiloxanes can be reacted with a cyclic anhydride or a dicarboxylic acid to provide carboxylic acid-functional polysiloxanes.
Plueddemann, U.S. Pat. No. 3,956,353, teaches that certain N-(aminoethyl)-aminoalkyl-substituted silanes can be reacted with 1 or 2 mols of a dicarboxylic acid anhydride to provide a zwitterion-substituted or a diacidamide-substituted silane, respectively.
Takemizawa et al., U.S. Pat. No. 4,075,167, have disclosed the reaction of a substituted maleic anhydride with an aminohydrocarbyl-substituted or an N-(aminoethyl)-aminohydrocarbyl-substituted silane or siloxane. In the later stages of this reaction, the use of an aliphatic acid anhydride in catalytic amounts or in reaction-medium amounts is allowed. The resulting maleimido group-containing organosilicon compounds are useful as photopolymerizable compositions.
Saam, in U.S. Pat. No. 3,440,261, discloses a method for making silanes and siloxanes containing at least one silicon-bonded N'-acyl-N-(aminoalkyl)-aminohydrocarbyl radical (herein also partially acylated diamine radical). However, the compounds of Saam are still amine-substituted compounds and the method of Saam is incapable of providing a silane or siloxane having fully modified diamine radicals, i.e. N,N'-diacyl-N-(aminohydrocarbyl)-aminohydrocarbyl radicals (herein also, fully acylated diamine radicals) or monocarboxylic acid salts of partially acylated diamine radicals.
Morehouse, U.S. Pat. No. 2,929,829, teaches that organosilicon compounds containing an acylamino group which is attached to a silicon atom through a polymethylene linkage that contains at least three carbon atoms can be prepared by the reaction of an organosilicon atom bearing an aminoalkylsilyl grouping with a monocarboxylic acid, or an ester, halide or anhydride thereof. Although the compounds of Morehouse are fully modified, full modification such as full acylation of diamine radical-containing organosilicon compounds, and the benefits attendant therewith, are not suggested.
Thus, while the art teaches reacting a silane or siloxane containing diamine radicals with various reactants to provide fully or partially derivatized diamine radicals, said fully or partially derivatized diamine radicals are still reactive, for example by way of residual amine radicals or by way of introduced reactive radicals, such as urea radicals, carboxyl radicals, etc. An improved method for modifying the reactivity of an organopolysiloxane which bears diamino radicals is therefore needed so that an even lower degree of amine reactivity is provided therefor without the introduction of other reactivities.